Why Not? Stop Overthinking Solo Travel

Maybe you've been thinking about a trip for months, looking at flights, reading about the destination, knowing roughly what's there. And still not booking. Or you've already been on the trip and running a calculation the whole time: how do I make this count? Was this worth it? Both versions have the same problem. The question you're asking doesn't close. It just generates more conditions.

In this episode, Damianne introduces the two-word question she's used for years, one that doesn't require a perfect reason to go, just the absence of a real blocker. With three stories from three very different decisions, she traces how the same question opened doors she couldn't have planned for, including thirteen years in a city she'd never seen before she arrived.

The "why should I go" question has a problem: it's designed for explanation, for optimization. It needs a good reason, and so it's easy to delay. Instead, you generate concerns. Address one, and another appears. The timing isn't right. The savings aren't there. Something at work needs you. 

Solo travel for women over 40 isn't really a logistics problem. It's a question. So we need to ask better questions.

In this episode:

• The cherry blossom calculation
• The question that keeps generating conditions
• Two words and how they work
• Off the main path in Sapa
• A pyramid in Tirana
• Thirteen years late

This episode is for you if:

• you've been looking at flights for a trip you haven't booked, and you're genuinely not sure what you're waiting for
• you travel solo and find yourself measuring the experience instead of just being in it
• you're a woman over 40 who wants to stop generating conditions and start deciding
• you've answered one concern about a trip only to find another one waiting in its place

Resources mentioned: 

Free workshop — freedomlookslikethis.com/training 

Make the trip decision in a small group with Damianne. Next session: June 6.

Transcript

SPEAKER_00 0:00

I found a pyramid in the south of the city, and it's this strange concrete structure. I love that kind of stuff. That's unexpected. So I had to walk up, intrigued by what I would find at the top and what sights would I be able to see. But the sun was directly overhead and I had no water. Most women think solo travel is about being brave or fearless. But it's really about letting go of the expectations holding you in place. This show is about what changes when you stop waiting and take yourself seriously, starting with intentional travel. I'm Damianne and this is Freedom Looks Like This. Let's get started. Maybe you've been thinking about a trip for months. Maybe even longer. You've looked at flights, you've read a few things about the destination. You know roughly what's there. And you keep looking, but you're not booking anything. Because something isn't quite right yet. Maybe you think it's the timing. Or maybe you don't quite have savings at the level that you would want. Or you think you need a bit more research before you can feel confident. Or maybe your excuse is that there is something coming up at work that you need to be there for. Here's a different version. You're on the trip and you're running a calculation in the background of your mind the whole time. So if you're going to be here for 10 days, you figure that you need to make them count. You need to see what's worth seeing. And eat what's worth eating. You've decided that you're going to get everything from this trip that it has to give because you flew this far or you spent so much money. Or maybe because you've been thinking about this trip for so long and you work hard to carve out this time. I talked about that before, about how I was in Japan and I went to Okazaki to see the Sakura in the evening. And it was raining, but that actually gave it a different ambience. There were lights all around because it was nighttime, and they had decorated the area for the festival. In fact, it was the first day of the festival. So I got to the riverbank and I was looking at all of the cherry trees and the cherry blossoms, and it was beautiful. But as I got closer, I realized that a lot of the buds were not open. So it was nowhere near the full bloom that people were advertising on social media. And I felt this sense of disappointment. But that's so funny because when I was looking at it from a distance, all I could see was the beauty. And all of a sudden, I found myself in this need to optimize the experience. Somehow the experience was less because the cherry blossoms were not in full blown. Has something like this ever happened to you? Have you arrived somewhere and found yourself spending more time measuring, evaluating the experience rather than being in it? Or maybe running the calculation of what's it worth? Was it really worth what I paid? And what I realized as I was on the train back from Okazaki, I realized that trying to optimize actually diminishes my experience. Always trying to get the most or get everything from my experience, to squeeze all the juice, if you will, that actually has a cost and it affects what we can experience in a trip. So when you're planning a trip, probably at some point you're thinking about why you should go to this particular country, this particular destination. Maybe also why should you go at the specific moment you're planning for? And those are all reasonable questions, right? Those are all the types of questions that we tend to ask ourselves before we make most decisions. Because we expect there to be a good reason for our actions and we want to feel justified. We want to be able to explain ourselves. And often when we have conversations with people, they expect it of us as well. What I notice about that question is it expects a good answer. And because of that, we find ourselves coming up with all of the roadblocks, all of the constraints, all of the reasons why we can't go on the trip. Somehow our why is not good enough often. And so we end up coming up with all the constraints, such as we need more money, or the timing's not right. And the thing with each of these constraints is that when we solve one of them, another one comes up. When the timing's right, maybe there's a problem with the destination. There's some security issue. I talked in the last episode about how the conditions and the constraints can keep changing as you think about going on a trip. As you answer one question, another one often appears. Part of the problem is the question why? By design, it's meant to produce reasons to keep asking. When you answer one question, it generates a new question. It doesn't really have a finishing point because there's always a better answer. In theory, you could do more research. You could always have more savings or find a better window. A lot of us maximizers have this problem where we don't just want to do the thing, but we want to do the thing in the best way possible. But the problem with that is that it keeps you in a state of preparation. Never taking the trip, but always planning for the trip. Never taking the trip, but always thinking about the trip. And this same mechanism also runs in the other direction on the trip. The question that shows up on the trip is often, how do I make this count? How do I get the most out of this? And that also doesn't have a satisfying answer. Because you could always do one more thing. You could always stay longer at the market, or you could ask the guide better questions, or maybe you could eat at one more restaurant or a different dish. So the question really doesn't close. Just like the why question, it generates more conditions, generates more things you need to do before the experience is complete. And of course, I'm talking about travel, but I bet that if you think about this, you can find the same pattern in many places in your life, not just in travel. Some questions are built to generate other questions so that you keep asking rather than doing. So today I want to offer you a different question. In my experience, it's a much simpler one. I've used it for years. I made a presentation on it at work in 2018. And I could really say that it has crafted the life that I have now. And it's only two words. It's the question, why not? That's it. So why not go to Albania? Why not hike off the main path in Saba, especially when I'm with a guide? Why not move to Prague? The reason why not works differently is that it doesn't require a perfect reason. It's not looking for perfection, it's just looking for the absence of a real blocker. And a real blocker is something specific. You can look at it directly and you can either solve it or you can accept it as something you can't change. A feeling of not being ready isn't actually a specific blocker. What do we mean when we talk about ready? It's the same thing when we talk about being uncertain whether we've researched enough or whether the timing could theoretically be better. Now, I know that why not can also be misread. I'm not asking you to ignore your hesitations or to be reckless. In fact, I think as women over 40, we need to tune in to our intuition more, to notice when we're feeling discomfort and to figure out where that's coming from, what's coming up for us. What I'm saying here is to look at the things that come up directly, not to ignore them, but to look at them directly. Because when you look at why not directly, neither one of two things happen. You'll realize it's not a blocker, or you'll realize that it is actually real and something you need to address. Often when something is not a blocker, we realize that really what we were trying to do was optimize. Really what we were doing was using it to delay. And then of course, if you figure out something is real, then you can actually do something about it. So here's an example of a real why not. So in March, I was in Vietnam and I went for a hike in Saba. I went with a guide, and at some point she said, Oh, do you want to stay off the path or do you want to go off the path and just walk amongst the rice terraces? And the answer was so clear to me. I knew what I wanted, but I had some hesitations. And the best way to quickly get to those hesitations was to ask, why not go off the main path in Sapa? And what it came down to was my fear of heights. I wasn't sure if I would be able to manage the hike and if there were going to be some inclines and it was unpaved. So, for example, if the path was fine-dust, that makes me really uncomfortable. Like all I can think of is falling. So I have a real concern about heights. And so I could ask the guide, oh, what's the path like? How much are we climbing? Having a specific issue that I could look at allowed me to get the information that I needed for me to solve it. And I also remembered that when I had gone on a previous hiking trip where I struggled with the path, all the guide had to do was hold my hand, and that gave me the confidence I needed to be able to carry on. So, with one why not questions in a few minutes, I felt very confident to be able to go on the walk off the beaten path. So that's the whole mechanism. That's the whole process. Right away, a real blocker got solved for me. If it's not real, it disappears once you look at it. When you ask the question, why not? you get to see what kind of blockers are they, real or imaginary? So what is yours right now? I asked you that last week. What is that trip that you've been circling? When you look at what's stopping you, what is it specifically? What's your answer to why have you not taken that trip? Or why not take that trip this year? Now, sometimes when you ask the question why not, you might be tempted to hide. It's possible even with a why not question. What that looks like is giving a generic answer that is not specific. So sometimes when I ask women, oh why not travel alone? the answer I get is safety. And I'm not trying to say that safety is not a real concern. But what I'm trying to say is safety is kind of impossible for me to address. So when you say safety, I'm gonna invite you to tease apart that a bit more. What do you mean by safety? Is it not knowing the rules in a place? Is it that you think you won't be able to cross the street without getting hurt? Is it that you're concerned about the flight and you have a fear of flying? Is it that you don't speak the local language of the place you want to visit and you're worried about how you'll get help if something happens? Do you have a medical condition that requires a certain access to healthcare that might not be possible? You can start to see that I can ask lots of questions to help you come up with that specific thing. So why not go on the trip this year? When I ask that question, think about all of the specific reasons, things we could actually hold in our hands and look at them and decipher and come up with a way to address them. It needs to be specific. Another clear example I have of using why not is when I went to Albania. I went to Albania because I wanted an adventure. I wanted movement and a change of scenery. And uh I find that when I travel, it's also sometimes a way for me to access rest and restoration. And that's what I needed. I needed a reset. I didn't have any strong reasons why Albania specifically, except that I'd been curious about it. But I had no research, I didn't know the history of the country. I knew that there was a direct flight from Prague. So I asked myself why not go to Albania for the weekend. And the only thing that came up was I was taking a class at the time, and if you missed a certain number of classes, you would be kicked out of the course. This was real because the time that my flight arrived was the same time as when the course would get started, and I didn't know what my data would be like on the go. But I hadn't missed any classes yet, and so I could afford to miss one class. And so I went. I went in March directly from Prague, and in Prague it was still early spring. The mornings were cold and I wore a light coat, and uh so I brought clothing similar to what I wore in Prague. Layers, thankfully. Because the March, late March in Tirana at that time, it was so warm. I was not prepared for the heat. I arrived on Friday. I went exploring on Saturday and I found a pyramid in the south of the city, and it's this strange concrete structure. I learned later that it was built as a monument to the communist era dictator. But there are these wacky off-kilter items around it, and I love that kind of stuff. That's unexpected. So I had to walk up the pyramid, intrigued by what I would find at the top and what sights would I be able to see. But the sun was directly overhead and I had no water. I came to Tirana with no itinerary, no research on the city. So there I was standing at the top of this whitish pyramid, looking out at a city that I knew almost nothing about. It's not at all a glamorous moment. I was hot and thirsty, and I was unprepared in every obvious way. But I was there. I was in a city I'd been curious about and had no strong reasons to avoid. And even though it was hot and a bit uncomfortable, I still enjoyed walking around this strange concrete place in the heat. And I was able to go inside for a moment to escape and cool down. I actually have very fond memories of Tirana. I ended up meeting some Baha'is and they invited me for dinner. They had some Albanian friends over, and so we just had a lovely evening together. I was just enjoying the new sights and sounds. I walked through a green space that was quite nice. There were lots of other people around, so it felt like early summer. It felt energizing actually. I went for a tasting menu that was quite affordable. I got Botox for the first time. So I had a great time on that trip. Isn't it so funny that sometimes when we're unprepared for something, it actually sets us up to have a delightful experience. I find that often. I was thinking about that recently because on that hike in Sapa, there were no restaurants around for lunch, and so I knew that we were going to be having a picnic lunch. At some point, the guide asked if I was hungry, and I told her yes. And then we kept walking and walking. Eventually, we got to a large stone along the path, and she asked if it was okay for us to stop there or to eat, because she didn't think there would be anywhere else for us to stop anytime soon. And I was like, yes, please, because I am starving. So we were in the middle of rice fields. There was maybe a shed in the distance and a farmer planting something. But we sat on our stone and she took out an umbrella which I had to carry. It made me think of the Caribbean how I would sometimes go for a walk with an umbrella. So we used an umbrella for some shade, but then she opened her pack and started cutting things. Now, when I had booked the tour, I'd been told that there would be a fried chicken lunch because the tour operator had asked if I was vegetarian or not. So I was expecting a fried chicken lunch. But what she made me instead was kind of like burn me. She cut up tomatoes and the cucumber and had some chicken, and she made me a very large sandwich. There was way too much bread, so I told her I just wanted some of the sandwich and some vegetables and chicken. And then for dessert we had rice crackers and mango. So I was sitting on this rock holding an umbrella, eating my picnic lunch, and just looking out at the rice terraces. And I had to remind myself how lucky I was. It made me think about my trip years earlier in 2008 to Banawi. And at the time when I went, everything was lush and green, and the rice terraces were filled with water. But it was very different here in Saba because really it looked like everything was in transition. Some of the crops had already been harvested, and the land looked like it was resting. I don't know anything about farming, even though my grandparents were farmers. But it looked like they were waiting for something to happen for the next cycle. So we walked for over two hours through the rice terraces. It was me, my guide, and her husband. That's a whole other story why her husband was on this trip. But anyway, it was the three of us, and her husband was usually way in front or way in the back of us on the phone, watching YouTube videos, I assume. And myself and the guide, we would talk occasionally, but we were mostly walking in silence. And I was really just taking in the scenery and also watching where I was putting my feet, to be honest, because some of those paths were sometimes rough, and I'm not that confident in unpaved, narrow paths. I really wished I'd actually brought my walking sticks. I should make a habit of bringing them on every trip. And again, at some point I needed help, and the guide noticed, and she held my hand and helped me down the path. And sometimes I said, I'm okay, I'm just building up my confidence for me to walk down this path that's quite steep, where I feel a bit unsteady. I was sometimes tempted to get on my bum and just swoosh down. I didn't have to resort to that, but there was a lot of nervous system regulation that I had to do. So every time the guide saw me stop, I think she thought that I needed help. And sometimes I did need help. But sometimes what I had to do was just take a deep breath, talk myself through the experience, and remind myself that I was okay. Because this experience was exactly what I wanted to be. Off the bidden path, to be just out in nature, and to really just be walking, actually. We walked for about four hours in total, and we saw almost no one in that time. The first time we actually saw people were when we got to the Sin Chai community village where we would get picked up to take me back to my hotel. This was a community, so there were lots of children around. There were actually mostly older people and children who I saw. And it's so funny with children, they're just living their lives, right? Walking around, playing d. My guide asked some children where they were going and they answered to buy candy. And I thought, how I like children everywhere. And I think what I really enjoyed about that experience is that I wasn't trying to catalog it. I wasn't trying to actually achieve anything. And there were no thoughts of optimization. I was in the moment. A bit tired. I did say to the guide at some point, like we're getting back at the perfect time because I'm getting ready to not walk anymore. And everything just aligned. It was actually one of my best days on the trip. I'm just noticing that now. Have you had that? Have you had an experience where you stopped managing everything and you were just in it? And later on you realized what a wonderful experience it was for you. Of course, you enjoyed it in the moment, but you were also able to reflect later and realize the wonder of it. And remember, what got me to walk through the rice terraces was that small question, why not? That made it a really easy decision. And I also have used that question with big decisions in my life. Moving to Prague was a version of this. I moved to Prague in 2013 and I'd never visited. I didn't know much about it. People kept telling me that there's good beer here. And when I said that I don't drink alcohol, they would say, oh well, there's also good bread, which I do eat bread. But I had no strong history with Czech culture. I didn't really even know where Prague was. I am kind of embarrassed to admit. But because I asked myself why not, and I had no strong nose, I came to Prague. And oh my goodness, I just realized that Prague is the place that I have lived the longest in my whole life. This year is 13 years since I moved to Prague. The only other place that I lived for 13 years was St. Lucia. And so Prague is going to be the place that I have lived the longest. Isn't that amazing? And I got here with the question, why not? That question opened up the door to something that I couldn't even have anticipated. Prague wasn't an obvious choice. I saw the opportunity, and that why not question allowed me to keep the door open, and I walked through it, and here I am. I had no idea when I arrived here that this city would be where I stayed for so long. I didn't know what it would give me, I didn't know what it would require of me. And I had no idea who is the person that I would become living here. I had no way to know that. But here's the thing, I didn't need to know any of those things in advance. That's been part of the excitement and part of the adventure. I love living in the center of Europe. I love easy access to other European countries. I love the architecture. I love how walkable this city is. I love that people prioritize life and living over just working. Oh my goodness, I love so many things about this city. This is why I'm still here. And this is why when I ask myself the question, why not move back to Ottawa? Why not move back to Canada? I get a long list, and many of those Prag satisfies. So across Albania and Zappa and lots of other places throughout, and it's 13 years in the Czech Republic, the question why not has served me very well. And I would like to share it with you. It's a question that doesn't require certainty or readiness or a perfect answer. It doesn't have the same expectations and pressure as the why question does. What it requires of you is to look honestly at what's actually stopping you, to look at it specifically, and to ask yourself: is this real? Is this solvable? Is this a real thing? Or am I just generating new conditions so I don't have to decide? And here's what I've noticed about this distinction over time. Every time you ask the question honestly and deal with what you find, that's another way of building evidence that you can be trusted with your own decisions. And the way you build a life is through a series of choices and decisions. The trip matters and why not allows you access to a trip more quickly, more definitively than asking the question why. Before you go on a trip, you might be asking yourself the question, can I handle what I'll encounter there? And as I say every time, that question can only be answered by going on the trip. Once you're there, once you've gone, the question becomes something different. And it becomes, what's next? What do I do now that I've done this? That's a question that belongs with a woman who chooses herself. That's also one of the shifts for us to move to asking ourselves better questions. Those better questions are what helps us integrate what we experience into our lives. So here's my invitation for you this week. Name one trip you've been circling. It's the trip that keeps coming up when you think about where you want to go. You might have that trip from last week if you did the exercise. You've likely mentioned it to a friend before, or you've looked up flights and then closed the tab. Remember, we're naming that place specifically. It's not a region or a vague idea, but it's a specific country, even better if you can come up with a city. So now this is the new part. Even if you've already done the exercise last week, listen up. Now I want you to write down every why not you can think of, every single one of them. And then for each one, you get to ask, is this solvable? And if it is, solve it. If it's something that you can solve in the next 10 minutes, even partially, do it now. You maybe you need to send an email or look up a visa or book the guide. Solve the solvable problems because that also gets you closer to going on your trip. And if you're ready to level up, then here's your invitation. Open up your calendar and pick a window. Pick a window when you're actually going to go on that trip. If something in this episode landed for you, I'd love to hear what your why not is. What's the why not that you're sitting with right now? Or what came up when you did the exercise? You can reach me at contact at freedomlookslikehis.com. And if you're ready to move from circling to deciding, I have a free workshop on June 6th that walks you through this process with me in a small group. Find it at freedomlookslike this dot com forward slash training. Come and have some fun with us with a whole group of women asking the same sorts of questions. I'll be sharing more details about it as time goes on.